Publication Type Journal Article
Title Wittig Reaction: Domino Olefination and Stereoselectivity DFT Study. Synthesis of the Miharamycins Bicyclic Sugar Moiety
Authors Vasco Cachatra Andreia Almeida Joao Sardinha Susana D. Lucas Ana Gomes P. D. Vaz M. Helena Florencio Rafael Nunes Diogo Vila-Vicosa Maria Jose Calhorda Amélia P. Rauter
Groups HC
Journal ORGANIC LETTERS
Year 2015
Month November
Volume 17
Number 22
Pages 5622-5625
Abstract 2-O-Acyl protected-d-ribo-3-uloses reacted with [(ethoxycarbonyl)methylene]triphenylphosphorane in acetonitrile to afford regio- and stereoselectively 2-(Z)-alkenes in 10-60 min under microwave irradiation. This domino reaction is proposed to proceed via tautomerization of 3-ulose to enol, acyl migration, tautomerization to the 3-O-acyl-2-ulose, and Wittig reaction. Alternatively, in chloroform, regioselective 3-olefination of 2-O-pivaloyl-3-uloses gave (E)-alkenes, key precursors for the miharamycins bicyclic sugar moiety.
DOI http://dx.doi.org/10.1021/acs.orglett.5b02849
ISBN
Publisher
Book Title
ISSN 1523-7060
EISSN 1523-7052
Conference Name
Bibtex ID ISI:000365462900028
Observations
Back to Publications List